1. Field of the Invention
The present invention relates to the manufacture of N-(substituted)-3-aminoacrylonitriles. In particular the invention relates to the manufacture of compounds of the formula N(R.sub.1 R.sub.2)--CH.dbd.CH--CN where R.sub.1 is alkyl, phenyl, phenyl substituted with alkyl and/or --NH.sub.2 groups, or --(CH.sub.2).sub.n --NH--CH.dbd.CH--CN and R.sub.2 is hydrogen or alkyl with the proviso that when R.sub.1 is --(CH.sub.2).sub.n --NH--CH.dbd.CH--CN R.sub.2 is hydrogen, n being 1 to 8.
2. Description of the Prior Art
Processes for the manufacture of N-(alkyl)x-3-aminoacrylonitriles, also known as alkyl-beta-cyanovinylamines, are known. For example in U.S. Pat. No. 3,001,995, which issued Sept. 26, 1961, E. J. Frazza et al disclose a process in which beta-chloroacrylonitrile is reacted with an amine, e.g., dimethylamine, in an inert reaction medium preferably in the presence of a hydrogen chloride acceptor. As exemplified by Frazza et al dimethyl-beta-cyanovinylamine was subsequently obtained, when the amine was dimethylamine, in 77% yield by distillation at 93.degree.-99.degree. C. at 0.6-1.0 mm Hg pressure and n-butyl-beta-cyanovinylamine was obtained, when the amine was butylamine, in two fractions giving a total yield of 47% by distillation at temperatures of up to 121.degree. C. It has also been disclosed in Chemical Abstracts 76 45512d (1972) in an abstract of an article by R. G. Kostyanovskii et al that cis-beta-(di-tert-butylamino)acrylonitrile may be obtained from cyanoacetylene in 7 days in 66% yield by a stereospecific reaction at room temperature in the absence of solvent. A process for the manufacture of N-(dimethyl)-3-aminoacrylonitrile from acrylonitrile in less than 50% yield is also known.
N-(R.sub.1 R.sub.2)-3-aminoacrylonitriles have various uses. For example, they may be polymerized with other ethylenically unsaturated monomers to give copolymers containing basic centers. Such copolymers find utility in the field of synthetic fibers when acid dyes are used as well as in ion exchange resins and oil additives.